---
title: 'Deployment Strategist at Probook'
canonical: 'https://feeny.ai/job/deployment-strategist-probook-manhattan-5cp16xgr8v3s'
type: 'job'
last_seen: '2026-09-09'
---

# Deployment Strategist at Probook

- **Company:** Probook
- **Location:** Manhattan, NY
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-09-04
- **Last confirmed live:** 2026-09-09
- **Apply:** https://jobs.ashbyhq.com/probook/b768ad07-8d80-4c7c-a854-1507b60d4571

## Job description

## ABOUT PROBOOK

Probook is the AI Operating System for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate.

Our impact is real. Dispatching the right technician to the right job can mean the difference between a $300 "band-aid" fix and a $20,000 system replacement. By automating previously high-touch workflows around-the-clock, Probook ensures a consistent customer experience without the need for 24/7 live staffing. We unify our customers' processes into a single, scalable platform, giving businesses one place to run their entire dispatch operation.

## THE OPPORTUNITY

The Deployment Strategist owns the post-sale technical and operational journey for new customers. This is a project-ownership role: you are responsible for hitting deployment milestones and go-live dates, not just holding a relationship. You sit between the sales handoff and the customer success team, and you are the person accountable for a customer's first experience actually running on the product.

## WHAT YOU'LL DO

- Run kickoff calls and set expectations with new customers on scope, timeline, and what a successful deployment looks like
- Build and manage a deployment project plan, keeping timelines, stakeholders, and internal teams aligned to hit go-live dates
- Present deck overviews and progress updates to customer stakeholders, from operators to executives
- Troubleshoot and resolve technical and workflow issues that come up during implementation, without routing them elsewhere
- Train end users and ensure the product is actually being adopted, not just installed
- Identify and flag risk early when a deployment is falling behind, or a customer is disengaged
- Hand off cleanly to the Customer Success team once a customer is live and stable
- Provide feedback to product and engineering based on patterns seen across deployments

## WHAT WE'RE LOOKING FOR

- 2+ years in an implementation, deployment, or onboarding role at a SaaS company (title may vary: Implementation Specialist, Onboarding Manager, Deployment Strategist, Technical Onboarding Manager)
- Direct, hands-on experience running the full implementation lifecycle for a software product — not just supporting one
- Comfortable running structured kickoff calls, presenting to stakeholders, and managing a project plan independently
- Track record of hitting deployment deadlines and can speak to specifics (number of implementations run, average time-to-go-live, customer count)
- Strong ownership instinct — when something breaks, or a customer is stuck, you solve it yourself rather than escalating
- Comfortable learning a technically complex product quickly and becoming the go-to expert on it
- Strong written and verbal communication; able to translate technical detail into plain language for non-technical stakeholders
- Organized and deadline-driven; able to run multiple concurrent deployments without dropping details
- Based in or willing to relocate to the NYC area; this is a five-day-a-week in-office role

## WHY PROBOOK

- The Tailwinds: $700B industry with clear tailwinds: AI adoption, labor shortages, and generational transitions creating demand for operational modernization. We are defining the category, not fighting for share.
- The Traction: $XXM ARR in 18 months. Product-market fit proven; now we're scaling.
- Funding: $40M raised from Sequoia and Andreessen Horowitz
- The Team: >60 people, our founding team comes from the space and has spent thousands of days onsite with our customers. We live the space. We're also becoming one of the most talent-dense start-ups in NYC (MIT, Harvard, UPenn M&T, Waterloo, Citadel, Palantir).

## COMPENSATION & BENEFITS

- Equity: Meaningful early-stage equity.
- Salary: $110,000 - $130,000 (Can flex depending on YOE)
- Health: Comprehensive medical, dental, and vision.
- Perks: $500 monthly Ramp card for commuting, meals, gym, etc. (plus $25 in nightly meal delivery credit) and really good office snacks.
- Access: Direct access to world-class investors and advisors.

## About Probook

## Company Overview
- **One-liner**: Probook builds an AI-powered operating system for home services companies, automating dispatch, lead management, and customer communication to help trades businesses scale.
- **Entity Type**: Private (raised $40M Series A)
- **Headquarters**: New York, NY, United States
- **Founded**: 2022
- **Founders**: Ben Cervantez (Co-Founder), George Eliadis (Co-Founder & CEO), Lewis Zhang (Co-Founder & CTO)

## Core Business
- **Primary industry**: Home Services Software / AI / Vertical SaaS
- **Target customers**: Home services companies (HVAC, plumbing, electrical, pressure washing, etc.) — primarily mid-market and enterprise operators with multiple locations and large dispatch teams
- **Mission or purpose statement**: Built by the trades, for the trades — to solve the hardest operational problems in home services with AI.

## Products & Services
- **Probook AI Operating System**: An all-in-one platform that automates dispatch, lead capture, outbound booking, and customer communication. Key features include:
  - **AI Dispatch**: Automatically matches technicians to jobs based on skills, location, and history; forecasts ETAs.
  - **Lead Capture & Chat Automation**: Handles 90% of customer chats automatically, capturing every lead from voice calls and web.
  - **Outbound Booking**: Automatically fills the board by working unsold estimates and outbounding to past customers.
  - **Full Context CRM**: All customer interactions in one place, with full history checks before jobs hit the board.
  - **Integrations**: Works natively with ServiceTitan and other industry tools.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (private company)
- **Key Metric**: Raised **$40M** in funding from Sequoia Capital and Andreessen Horowitz (a16z) — announced on their homepage.
- **Notable Investors/Partners**: Sequoia Capital, Andreessen Horowitz (a16z)
- **Growth Signals**:
  - 3,518 LinkedIn followers (+2.8% monthly growth)
  - Website traffic: ~10,906 monthly visits (+5.2% monthly, +202.9% yearly)
  - Customer results cited: 20%+ increase in average ticket, 82% true booking rate, 22 → 10 dispatchers, 15,000+ calls/month handled
  - Describes itself as "the fastest-growing AI startup in New York"
  - Backed by two of the most prestigious VC firms in the world

## Competitive Advantages
- **Domain expertise**: Founders grew up in the trades; CEO George Eliadis ran a pressure washing business for 6 years. The team "came up in the trades" and deploys in person, configuring alongside customers.
- **Talent density**: Engineering team includes multiple ICPC World Finalists and IMO Gold Medalists — described as "more talent-dense than early Ramp."
- **GTM/CS expertise**: Leadership from Procore, Zocdoc, and other vertical SaaS leaders.
- **Focus on dispatch as the core**: Unlike other AI vendors, Probook is built around dispatch — the operational heart of home services — making it uniquely sticky.

## Strategic Focus
- **Category creation**: Building the "AI operating system for home services" — a new category-defining product.
- **Vertical depth**: Deep integration with existing tools (ServiceTitan) and workflows, rather than a horizontal AI play.
- **Scaling the team**: Actively hiring across engineering, sales, customer success, and operations to fuel rapid growth.
- **In-person deployment**: Hands-on, high-touch implementation to ensure outcomes — "stay on the hook for the results we sell."

## Why Work Here
- **Culture**: Described as a "small, cracked team" with diverse professional backgrounds. The company emphasizes working on "harder and more real" problems than quant or big tech.
- **Talent density**: Opportunity to work alongside world-class engineers (ICPC finalists, IMO gold medalists) and operators from top vertical SaaS companies.
- **Impact**: Early-stage startup with a clear product-market fit and massive market opportunity — employees can have outsized influence.
- **Location**: Based in New York City (office in NYC). Roles are listed as full-time and in-office (New York).
- **Perks/Notable**: Backed by Sequoia and a16z; strong engineering culture; focus on solving real problems for real businesses.
- **Open roles** (as of latest data): Founding Design Engineer, Senior Software Engineer, Staff Software Engineer, Sales Development Representative, Head of Implementation, Enterprise Customer Success Manager, FDE, Founders Associate, Business Operations Lead, Founding GTM Recruiter, Enterprise Account Executive, Solutions Consultant, Executive Assistant, Head of Talent.

## Sources
1. [probook.ai](https://www.probook.ai/)
2. [probook.ai/company](https://www.probook.ai/company)
3. [probook.ai/careers](https://www.probook.ai/careers)
4. [jobs.ashbyhq.com/probook](https://jobs.ashbyhq.com/probook)
5. [linkedin.com/company/probook-ai](https://www.linkedin.com/company/probook-ai)

## Other roles at Probook

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- [Senior Product Marketing Manager](https://feeny.ai/job/senior-product-marketing-manager-probook-manhattan-4qab6c8d49gr) — Manhattan, NY
- [Enterprise Customer Success Manager](https://feeny.ai/job/enterprise-customer-success-manager-probook-manhattan-6zvabj1xgfzk) — Manhattan, NY
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- [Head of Talent](https://feeny.ai/job/head-of-talent-probook-manhattan-7hynck42xfdr) — Manhattan, NY
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